N-(2,2-dimethoxyethyl)-N-methyl-N-phenylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2,2-dimethoxyethyl)-N-methyl-N-phenylamine
• 英文别名: N-(2,2-dimethoxyethyl)-N-methylaniline
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: DOUCWVQPDVIRJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氨基乙醛缩二甲醇 、 氯苯 在 bis(acetylacetonate)nickel(II) sodium hydride 、 sodium t-butanolate 、 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到N-(2,2-dimethoxyethyl)-N-methyl-N-phenylamine
  参考文献：
  名称：

  Nickel(0)/Dihydroimidazol-2-ylidene Complex Catalyzed Coupling of Aryl Chlorides and Amines

  摘要：

  A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.

  DOI：

  10.1021/jo016352l

文献信息

• Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines
  作者：Eric Brenner、Raphaël Schneider、Yves Fort

  DOI：10.1016/s0040-4020(99)00788-7

  日期：1999.10

  The reaction of aryl chlorides with secondary amines or piperazines in the presence of an in situ generated liganded nickel catalyst gives arylamines in good yields. Our process provides a mild, convenient and cheap method of arylamination starting from readily available substrates. (C) 1999;Elsevier Science Ltd. All rights reserved.
• Nickel-catalysed amination of aryl chlorides using a dihydroimidazoline carbene ligand
  作者：Benoı̂t Gradel、Eric Brenner、Raphaël Schneider、Yves Fort

  DOI：10.1016/s0040-4039(01)01079-6

  日期：2001.8

  A new arylamination protocol has been developed using a catalyst combination prepared from Ni(acac)(2) associated to a sterically hindered dihydroimidazoline carbene ligand. A high efficiency was attained using, in most cases, only 2 mol%. Ni/carbene clusters. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Nickel(0)/Dihydroimidazol-2-ylidene Complex Catalyzed Coupling of Aryl Chlorides and Amines
  作者：Christophe Desmarets、Raphaël Schneider、Yves Fort

  DOI：10.1021/jo016352l

  日期：2002.5.1

  A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.